Selective herbicides based on a substituted phenyl sulfonyl amino carbonyl triazolinone

ABSTRACT

The present invention relates to selective-herbicidal compositions, characterized in that they contain an effective amount of the compound 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula (I)                    
     and/or of salts of the compound of the formula (I), and to the use of these compositions for the selective control of weeds in crops of cereals, in particular crops of wheat, and to methods for the selective control of weeds in crops of cereals by applying the compositions together with surfactants and/or customary extenders.

FIELD OF THE INVENTION

The invention relates to the use of the known compound2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneof the formula (I) shown below—alias methyl2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)-carbonyl]-amino]-sulphonyl]-benzoate(CAS-Reg.-No.: 145026-81-9)—and its salts, in particular its sodium salt(CAS-Reg.-No. 181274-15-7), for the selective control of weeds in cropsof useful plants, in particular for controlling problematic weeds incereals.

BACKGROUND OF THE INVENTION

Substituted phenylsulphonylaminocarbonyltriazolinones such as, forexample, the compounds2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-butoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-ethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-isopropoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,2-(2-ethoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-propoxy-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneand2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-ethyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneand their salts, processes for preparing these compounds and their useas herbicides are the subject of earlier patent applications (cf. EP-341489, EP-422 469, EP-507 171, U.S. Pat. No. 5,534,486). The individualabovementioned substituted phenylsulphonylaminocarbonyltriazolinoneshave a molecular structure which is very similar to that of the compound(I) to be used according to the invention but, in contrast to thiscompound, they show shortcomings in their activity or activity gaps inthe case of certain weeds.

SUMMARY OF THE INVENTION

Selective-herbicidal compositions comprise an effective amount of thecompound2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one.

DETAILED DESCRIPTION

Surprisingly, it has now been found that the compound2-(2-methoxycarbonylphenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(I) and salts thereof, in particular the sodium salt of the compound ofthe formula (I), in comparison with the abovementioned structurallysimilar compounds, show considerably stronger activity against someweeds in cereal crops which are difficult to control, combined with verygood compatibility with cereal species, such as, in particular, wheat,and are therefore particularly suitable for the efficient and selectivecontrol of weeds in cereals, in particular in wheat. The activity gapsobserved with the abovementioned comparative compounds which are closelyrelated to (I) do not occur in the weed spectrum of the compound (I) andits salts.

The invention provides selective-herbicidal compositions, characterizedin that they contain an effective amount of the compound2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneof the formula (I)

and/or of salts of the compound of the formula (I), in particular oftheir sodium salt [referred to as “(I)-Na-salt” in the use examples].

The invention furthermore provides the use of the compound2-(2-methoxycarbonylphenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneof the formula (I) and/or of salts of the compound of the formula (I),in particular of its sodium salt, for the selective control of weeds incrops of cereals, in particular in crops of wheat.

The invention furthermore provides a method for the selective control ofweeds in crops of cereals, in particular in crops of wheat, which ischaracterized in that the compound2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneof the formula (I) and/or salts of the compound of the formula (I), inparticular its sodium salt, is/are applied with surfactants and/orcustomary extenders in crops of cereals.

The compound of the formula (I) and its Na salt are already known (cf.U.S. Pat. No. 5,534,486—Examples 72 and 320).

The compound of the formula (I) and its salts have a broad herbicidalactivity. They can be used, for example, for controlling the followingweeds:

Dicotyledonous weeds of the orders: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Monocotyledonous weeds of the orders: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.

However, the use of the compound (I) and its salts is by no meanslimited to these orders but extends in the same manner to other plantsas well.

The compound of the formula (I) and its salts have strong herbicidalactivity and a broad spectrum of activity when used on the soil and onabove-ground parts of plants. They are suitable for the selectivecontrol of monocotyledonous and dicotyledonous weeds in monocotyledonouscrops, especially in cereals, in particular in wheat, both by thepreemergence and by the post-emergence method.

Problematic weeds which can be controlled particularly well with thecompound of the formula (I) and its salts, in particular its sodiumsalt, and whose control is less likely to succeed with both conventionalherbicides and more recent compounds of a similar molecular structureare, in particular, Agropyron, Alopecurus, Amaranthus, Apera, Avena,Bromus, Capsella, Erysimum, Lolium, Phalaris, Poa, Setaria, Sinapis andThlaspi.

The compound of the formula (I) and its salts, in particular its sodiumsalt, can be converted into the customary formulations, such assolutions, emulsions, wettable powders, suspensions, powders, dusts,pastes, soluble powders, granules, suspension/emulsion concentrates,natural and synthetic materials impregnated with active compound, andvery fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Suitable liquid solvents areessentially the following: aromatic hydrocarbons, such as xylene,toluene or alkylnaphthalenes, chlorinated aromatics, such aschlorobenzenes, chlorinated aliphatics, such as chloroethylenes ormethylene chloride, aliphatic hydrocarbons, such as cyclohexane orparaffins, petroleum fractions, mineral and vegetable oils, alcohols,such as butanol or glycol and also their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, and also water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,and also synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifying and/or foam-forming agents are: forexample non-ionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates aswell as protein hydrolysates; suitable dispersing agents are: forexample lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes, such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For the control of weeds, the compound of the formula (I) and its salts,as such or in the form of their formulations, can also be used asmixtures with known herbicides, finished formulations or tank mixesbeing possible.

Possible components for the mixtures are known herbicides, for exampleamidosulfuron, bentazon, bromoxynil, carfentrazone(-ethyl),cinidon(-ethyl), clodinafop(-propargyl), clopyralid, chlorsulfuron,chlortoluron, cyclosulfamuron, 2,4-D, diclofop(-methyl), difenzoquat,diflufenican, floransulam, flupyrsulfuron(-methyl, -sodium),pyraflufen(-ethyl), ethoxyfen, fenoxaprop(-ethyl),fluoroglycofen(-ethyl), flupropacil, fluroxypyr, iodosulfuron,isoproturon, mecoprop, metosulam, metribuzin, metsulfuron(-methyl),pendimethalin, prosulfocarb, pyridate, sulfosulfuron,thifensulfuron(-methyl), tralkoxydim, triasulfuron, tribenuron(-methyl),trifluralin.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, are also possible.

The compound of the formula (I) and its salts can be used as such, inthe form of their formulations or in the use forms prepared therefrom byfurther dilution, such as ready-to-use solutions, suspensions,emulsions, powders, pastes and granules. They are used in the customarymanner, for example by watering, spraying, atomizing or scattering.

The compound of the formula (I) and its salts can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 1 kg of active compound per hectareof soil surface, preferably between 5 g and 0.5 kg per ha.

The use of the compound of the formula (I) and its salts can be seenfrom the following examples.

USE EXAMPLES

The compounds listed below are used as comparative substances in the useexamples:

2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-butoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(known from EP-507 171, U.S. Pat. No. 5,534,486—Example 40)

2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-ethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one-sodiumsalt (known from U.S. Pat. No. 5,534,486—Example 185)

2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-isopropoxy-2,4-dihydro-3H-1,2,4-triazol-3-one-sodiumsalt (known from U.S. Pat. No. 5,534,486—Example 259)

2-(2-Ethoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(in the claim of EP-507 171 and U.S. Pat. No. 5,534,486)

2-(2-Methoxyxcarbonyl-phenylsulphonylaminocarbonyl)-4-propoxy-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one(in the claim of EP-341 489 and EP-422 469 and also U.S. Pat. No.5,057,144)

2-(2-Methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-ethyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(in the claim of EP-507 171 and U.S. Pat. No. 5,534,486)

Example A

Post-emergence Test/greenhouse

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. The concentration ofthe spray liquor is chosen so that the particular amounts of activecompound desired are applied in 500 l of water/ha. After three weeks,the degree of damage to the plants is assessed in % damage in comparisonto the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100% total destruction

In this test, for example, the sodium salt of the compound of theformula (I) exhibits, at an application rate of 60 g/ha, very strongactivity (efficacy 80% to 100%) against weeds, such as, for example,Agropyron, Alopecurus, Avena, Bromus and Lolium, combined with very goodcompatibility with crop plants, such as, for example, wheat, whereas thecomparative compounds (A), (C), (D), (E) and (F) have considerablyweaker herbicidal activity and the comparative compounds (B) and (F) arenot entirely compatible with wheat. [“ai.”=“active ingredient”].

TABLE A Post-emergence test/greenhouse Application rate Active compound(g ai./ha) Wheat Agropyron Alopecurus Avena Bromus Lolium Comparativecompound 60  0  0  0 50  0  0 (A) Comparative compound 30 60 90 90 90 8090 (B) Comparative compound 60  0 60 70 50 70 70 (C) Comparativecompound 60  0 70 — 20 80 30 (D) Comparative compound 250  0 — 70  0 5050 (E) Comparative compound 60 20 50 50 40 50 30 (F) according to theinvention: (I)—Na-salt 60  0 100  90 80 95 80

Example B

Pre-emergence Test/greenhouse

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of the spray liquor is chosen so that theparticular amount of active compound desired is applied in 500 litres ofwater per hectare.

After three weeks, the degree of damage to the plants is tested in %damage in comparison to the development of the untreated control.

The figures denote:

0% no effect (like untreated control)

100%=total destruction

In this test, for example, the sodium salt of the compound of theformula (I) exhibits, at application rates of from 15 g/ha to 60 g/ha,very strong activity (efficacy 80% to 100%) against weeds, such as, forexample, Agropyron, Alopecurus, Avena, Bromus, Lolium, Poa, Setaria andSinapis, combined with very good compatibility with crop plants, suchas, for example, wheat, whereas the comparative compounds (A), (C), (D),(E) and (F) exhibit considerably weaker herbicidal activity and thecomparative compound (B) is not entirely compatible with wheat.

TABLE B1 Pre-emergence test/greenhouse Application rate Active compound(g ai./ha) Wheat Alopecurus Avena Bromus Lolium Setaria Comparativecompound 500 0 20  0 30  0  0 (A) according to the invention:(I)—Na-salt  30 0 95 90 90 80 90

Table B2 Pre-emergence test/greenhouse Application rate Active compound(g ai./ha) Wheat Agropyron Alopecurus Avena Bromus Lolium Poa SetariaComparative compound 30 0 50 70 70 70 — 80 70 (C) Comparative compound30 0 60 70 30 — 30 70 50 (D) according to the invention: (I)—Na-salt 300 90 95 90 90 80 95 90

TABLE B3 Pre-emergence test/greenhouse Application rate Active compound(g ai./ha) Wheat Agropyron Alopecurus Avena Bromus Poa AmaranthusSinapis Comparative compound 15 40 40 — 60 — 70 70 70 (B) Comparativecompound 15  0  0 40  0 20  0 70 70 (F) according to the invention:(I)—Na-salt 15  0 90 95 80 90 90 95 90

TABLE B4 Pre-emergence test/greenhouse Application rate Active compound(g ai./ha) Wheat Alopecurus Avena Bromus Lolium Setaria Comparativecompound 250 0 80  0  0 40  0 (E) according to the invention:(I)—Na-salt  60 0 95 90 95 80 90

Example C

Post Emergence Tests/outdoors

Under outdoor conditions, the sodium salt of the compound of the formula(I) was tested in winter wheat in Germany and France againsteconomically important weeds. The small-plot experiments were carriedout on cultivated land under agricultural use, with cultivation andclimate conditions which can be considered to be representative for theperiod of the trial. Areas with particularly extensive weed growth werechosen by way of preference.

The active compound was applied by the post-emergence method (spring)across the area by the spray method, with an average droplet size. Toproduce a useful preparation of active compound, the active compound wasformulated as 70 WP or 70 WG (70% w/w water-dispersible powder orgranules) and applied with customary amounts of water.

To assess the crop compatibility, from 1 to 8 weeks after the treatment,plant growth inhibitions or ailing of the leaf area were assessed in %damage in comparison to the development of the untreated control. Atdifferent intervals after the treatment, the herbicidal activity wasassessed as % reduction in comparison to the untreated control, based onthe weed development. The figures denote:

0%=no damage of the crops or no herbicidal effect,

100%=total destruction of the crops or the weeds.

The experiments which were carried out show that the sodium salt of thecompound of the formula (I) is particularly suitable for controlling theperennial species Agropyron repens, which is difficult to control, andthe annual species Alopecurus myosuroides, Apera spica-venti, Capsellabursa-pastoris and Sinapis arvensis in cereals.

[“% w/w”=per cent by weight]

TABLE C Post-emergence tests/outdoors (I)-Na-salt (42 g of a.i./ha to 45g of a.i./ha) Test plants Number of tests herbicidal effect (%)Agropyron repens 83 89 Alopecurus myosuroides 204 91 Apera spica-venti87 94 Poa annua 5 67 Capsella bursa-pastoris 6 100 Sinapis arvensis 4100 Damage to the crop (wheat) 439 2

Example D

Post-emergence Tests/outdoors

The sodium salt of the compound of the formula (I) was tested underoutdoor conditions in the main cultivation areas of winter wheat in theUSA (Pacific Northwest, North Central Area, Central Plains) againsteconomically important weeds. The design, the practice and theevaluation of the experiments corresponded to Example C. The activecompound was applied in autumn. Wetting of the plants was improved byaddition of commercial surface-active substances (SAS) in theconcentrations recommended by the respective manufacturer.

The tests show that the sodium salt of the compound of the formula (I)is particularly suitable for controlling Bromus species, Erysimumcheiranthoides and Thlaspi arvense in cereals.

TABLE D Post-emergence tests/outdoors (I)-Na-salt Number (42 g a.i./hato 45 g a.i./ha) Test plants of tests herbicidal effect (%) Bromussecalinus 24 95 Bromus tectorum 37 90 Erysimum cheiranthoides 10 89Thlaspi arvense 7 100 Damage to the crop (wheat) 78 2

Example E

Post-emergence Test/outdoors

The sodium salt of the compound of the formula (I) was tested underoutdoor conditions in an irrigation wheat growing area of the USA(California) against economically important weeds. The design, thepractice and the evaluation of the tests corresponded to Example D.

The tests which were carried out show that the sodium salt of thecompound of the formula (I) is particularly suitable for controllingPhalaris species in cereals.

TABLE E Post-emergence test/outdoors (I)-Na salt + SAS (42 g a.i./ha to45 g a.i./ha) Number herbicidal effect Test plants of tests (%) Phalarisminor 2 93 Phalaris paradoxa 8 99 Damage to the crop (wheat) 7  5

What is claimed is:
 1. A method for the selective control of at leastone weed selected from Agropyron, Alopecurus, Avena, Capsella, Erysimum,Lolium, Phalaris, Poa, Setaria, Sinapis, Thlaspi and combinationsthereof in a cereal crop comprising applying an effective amount of2-(2-methoxycarbonyl-phenylsulfonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneand/or salts thereof to said crop.
 2. The method of claim 1, whereinsaid crop is wheat.
 3. The method of claim 1, wherein said at least oneweed is selected from Agropyron, Alopecurus, Avena, Lolium, Poa, Setariaand Sinapis.
 4. The method of claim 1, wherein said at least one weed isAlopecurus.
 5. The method of claim 1, wherein said at least one weed isAgropyron.
 6. The method of claim 1, wherein said2-(2-methoxycarbonyl-phenylsulfonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneand/or salts thereof is applied at an application rate of 15 to 60 g/ha.7. The method of claim 1 wherein said at least one weed is Alopecurusand said crop is winter wheat.
 8. The method of claim 1 wherein said atleast one weed is Agropyron and said crop is winter wheat.
 9. The methodof claim 7, wherein said2-(2-methoxycarbonyl-phenylsulfonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneand/or salts thereof is applied as 70 WP or 70 WG formulation.